Controller; or DC

About the Company

America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences.

Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure.

Founded in 2024, Twenty Technologies ((Use the "Apply for this Job" box below).) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $138M from Accel, Caffeinated Capital, Friends & Family Capital, Point
72 Ventures, General Catalyst, and In‑Q‑Tel.

This role is based full-time in either our New York City office or our Washington, DC headquarters. Candidates currently based in the San Francisco Bay Area must be willing to relocate to NYC or the Washington, DC area.

As our first Controller, you will be the foundational leader of our accounting department. This is a "player‑coach" role designed for someone who wants to architect a sophisticated, high‑velocity finance function from the ground floor.

You will lead the development of our internal systems, controls, and automated workflows, ensuring we are navigating hypergrowth optimally. A key part of this role involves collaborating with and overseeing our external partners to ensure our financial engine is running at peak efficiency. You will anticipate the requirements for scale and leverage AI‑native tools to build a modern, lean, and highly accurate department.

• Own Accounting and Financial Operations: Lead all accounting functions, from annual to day‑to‑day workflows, ensuring accuracy, efficiency, and timeliness. You will own the procure‑to‑pay lifecycle.
• Build for Scalability: Identify, propose, and implement solutions to automate and optimize processes. Work with our team to maintain (or reduce) overhead requirements, even as transaction volumes 10x.
• Future Audit Readiness: Prepare Twenty for future audits by building the required roadmap and timing of all necessary requirements.
• External Management: Manage and build relationships with all external partners, including tax, bookkeeping, vendors, government partners, and auditors.
• Systems Optimization: Explore and implement tools like Ramp AI and API connections between internal systems to streamline workflows.
• People & Policy: Develop internal processes, such as expense and procurement policies; build strong relationships with company leaders, as well as trust with all employees.
• Special Projects: Support a range of initiatives, which may include real estate planning, variable compensation analysis, cash management policies, and contracting.
• Treasury: Monitor corporate cash balances and manage treasury movements to ensure the company remains optimized across liquidity and yield.
• Cross‑Functional Support: Step outside the normal job description to own key workflows that help a cross‑functional team scale rapidly—e.g., assisting with Sales Ops, Legal, HR, and Office operations.

• Accounting
  
  Experience:
  
  8+ years of accounting experience, including time in Big 4 (or equivalent) audit and high‑growth technology startups.
• Government Contracts
  
  Experience:
  
  Experience with DCAA compliance and government contracts.
• Credentials: Current or former CPA is favored, but not required.
• Execution‑Oriented: You believe that what sets high‑performing teams apart is their ability to execute.
• Highly Detail‑Oriented: You believe that formatting is a valuable tool for cross‑functional communication, not a burden. You sweat the details because you know they matter.
• Concise Communication: Ability to distill information for executive audiences.
• Prioritization: You understand the operational realities of a high‑growth startup, knowing when speed must beat perfection and when a task is more efficiently handled manually.
• Financial Systems Expertise: Experience implementing and managing modern financial systems (e.g., ERP, spend management,…